Walt Disney once said, "All our dreams can come true, if we have the courage to pursue them." And 28-year-old singer/songwriter Andy Grammer is a perfect example of just that. Getting his start as a street performer in Santa Monica, the pop singer spent three years showcasing his talents to anyone willing to listen. After countless hours of pounding the pavement, Grammer's hard work finally paid off when his single "Keep Your Head Up" hit the radio.

Currently on tour with Train, Grammer took some time out of his demanding schedule to chat with New Times about staying positive, connecting with fans, and doing a music video with The Office's Rainn Wilson.

New Times: Let's start from the beginning. You began as a street performer, is that correct?

Andy Grammer: Yeah! I'd take my guitar, set out an open guitar case and try to sell some CDs out in Santa Monica, California.I did it for three years. It was pretty cool, better than a real job, ya know? [laughs] I mean, I'd stay out there for long hours and whatnot. But it was still better than being a waiter.

That's a pretty intense thing to do, though, and I'm sure it didn't come without rejection. How did you manage to stay positive through all of that?

Well, it is pretty grueling. But there is still that satisfaction of someone buying a CD because they happened to walk by and liked you. Which is pretty validating as an artist in the early stages. So it was equally shitty and validating. Like, one point more validating than shitty at least. [laughs]

I can't even imagine. So at what point did you get "discovered" per se?

Well, I had been out therefor a while, and [my now manager] Ben Singer came out and saw me, and he liked what I was doing. We started working together, and then I recorded "Keep Your Head Up." That's when things really started to move.

You have Rainn Wilson [of The Office] in that video. How did that all come together?

Yeah! He's great. He had just written a book with my old roommate called Soul Pancake.

Oh my God! I love that book.

Isn't it awesome? It's so great. And I had known him a little bit. So I took him out to lunch and begged him to be in the video. And he agreed, which was totally awesome. I was so psyched.

All of this happened pretty fast for you. What's that like?

Well, all the stuff that everyone knows about. But I've been playing music forever. Three years on the street isn't superfast, though. [laughs] But yeah, to go from having the song hit the radio and now to be on my third single, yeah, that's pretty fast and crazy.

Do you ever wake up and have those "Holy shit, is this really happening?" type of moments?

Definitely. But it's also a lot of hard work, so it's a little bit of both. You definitely pinch yourself a lot, but you're also like this is what you've wanted. So it's a weird duality.

And is this what you wanted to see happen with your career? Did you have any idea that this was in the cards for you?

Yeah, I mean I don't think dreams can be too specific. Like, you can't be like, "I want to be going on tour with Train" [laughs] That's just insane. You can't dream that. But you can say, "I'm pretty sure this is what I'm supposed to be doing, and I'm going to go after it." In one sense, this had to happen because it was my plan. But in another sense, it's almost so ridiculous that it worked. To go from playing on the street to this is just crazy.

Has a lot changed for you?

My audience definitely. It's a large audience filled with people who know my music, and that's just pure bliss.

What's the best and worst part about being constantly on tour?

Well, if you're doing it at all right and successfully, you don't sleep very much. In the last five days, the longest block of time I've gotten to sleep is probably around four hours. So that's pretty crazy. This is a pretty chilled-out day for me, though, 'cause I just got off the plane and I was able to sleep for two hours. But that's probably all I will get until the next day. But the best part about it is that there is no other way to get in front of this many people in such a short amount of time.

The music industry is constantly changing. Do you think it's easier or more difficult for artists nowadays?

Well, I think it's more difficult to reach mass audiences. But that's not necessarily a terrible thing, because it's easier to reach niche [audiences]. Like, I think it's easy to be a musician who makes $40,000 a year. And that's an amount of money you can live off of. Which isn't bad at all. Ya know? It went from one person who was getting on the radio and making a bajillion dollars to 20 people who can all get heard.

Like, the rock star who is going to trash hotel rooms and not care because they have so much money and don't know what to do with it doesn't exist anymore. But did we really need that? [laughs] I don't need to trash my hotel rooms, so that's not a huge concern. [laughs] I think it's hard to figure out how to monetize. I don't think it's good or bad, it just is. There is so much more recording equipment that's cheaper, and so many people can have it in their hands. It makes you wonder how much good music did we lose or not get to hear because it was too expensive for people to create. I'm not against it -- there's positive and negative sides to it all -- it's all just a big jumble of stuff happening in the music world. Nobody really knows what's going to happen with it, which is funny.

A big part of the music industry right now is EDM, which you either love or hate. Is there a music trend happening at the moment that you just can't stand?

Well, while I'm not opposed to using it; I think four-on-the-floor is a little overused right now. I haven't used it in a song yet, but I probably will, and then I'll end up eating my words later on for it. [laughs] But I just think there is a lot of it out there right now.

Do you have any plans of working on your next album?

This current tour, I have been writing a lot. Putting together a bunch of songs to get something going. It's hard to write on the road, though, but I just have to do it.

You find it's more difficult to write on the road as opposed to being at home?

Yeah. Just 'cause you like get into the zone, but then all of a sudden you have to stop to sign some posters [laughs] or run out and meet people. Which is fun. But not when it's interrupting something creative. It's hard to balance that on the road.

Back in the day, meeting or talking to your favorite musicians on tour was unheard of. But now with Twitter, things have changed, and you're one of those musicians who is so interactive with their fans. What's that like? How do you feel about this accessibility?

I think it's pretty cool. You can go on Twitter, and your fans can tell you what they thought. You can tell whether they had a good time, and if they didn't, they will tell you. And then you can reach out to them on a personal level and figure out why. Also, every night I'll have a couple of people tweet at me, and then I'll bring them backstage at the show.

Wow. Really?

Yup. I'll just close my eyes and scroll down the @replies, stopping at random. Then I'll send them a direct message inviting them backstage.

Wow. I mean, that doesn't ever get crazy? Any superfans do anything over the top ever?

[laughs] No, no. Everyone is pretty cool to me.

You already have a few hit singles under your belt. You're doing large tours. So, what's next for you?

You know, it's funny. What I'm just hoping for is a bunch more great songs. When you're on tour with Train, they have so many great songs. Like, great songs. Ultimately, if you're a musician, I think that's what your goal should be. How do you amass a catalog of amazing songs? When you go to a Train show and they start playing a song, the crowd just erupts because it's provided them with such happiness, just that one song. And then they go into the next one, and it's like that one did too. Oh my God. So, in 20 years from now, I'd just like to have so many songs that have done people well.